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Diversification of Trifluoromethylthiolation of Aromatic Molecules with Derivatives of Trifluoromethanesulfenamide
Author(s) -
Horvat Monika,
Jereb Marjan,
Iskra Jernej
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800551
Subject(s) - chemistry , reagent , trifluoroacetic acid , triflic acid , dichloromethane , electrophile , reactivity (psychology) , medicinal chemistry , molecule , organic chemistry , solvent , stereochemistry , catalysis , medicine , alternative medicine , pathology
Trifluoromethylthiolation of aromatic compounds with different electrophilic reagents of the type ArNHSCF 3 was studied in the presence of triflic acid as an activator. The effect of the reagent structure on the reactivity was studied with three different reagents: PhNHSCF 3 (H/SCF 3 , 1a ), 4‐ClC 6 H 4 NHSCF 3 (Cl/SCF 3 , 1b ) and C 6 F 5 NHSCF 3 (F 5 /SCF 3 , 1c ). p ‐Chloro substituted reagent 1b was more stable than the unsubstituted 1a and was the most effective because it could not react by trifluoromethylthiolation of itself. This reaction was the most important side reaction of 1a . The pentafluoro derivative 1c was less reactive. Solvent played an important role in the transformation and, depending on the substrate, dichloromethane, hexane or trifluoroacetic acid gave the best yield of various trifluoromethylthiolated aromatic molecules (63–98 %).